Dimethylformamide → Benzenamine, 3-ethynyl-

Participants

Reaction Conditions

Reaction Steps

A 250 ml round bottomed flask, fitted with refrigerator, under a nitrogen stream, is loaded with 3-bromoaniline (2 ml), dimethylformamide (10 ml), trimethylsilylacetylene (3.4 ml), 1,1,3,3-tetramethyl guanidine (2.5 ml), CuCl (3.6 mg), PdCl2 (9.7 mg) triphenyl phosphine (58 mg), in this order. The mixture is heated to 55°-57° C. keeping this temperature until completion of the reaction. H2O (50 ml) and ACOEt (50 ml) are added at a temperature of 35°-30° C. The organic phase is evaporated to dryness and the residue is dissolved in CH3OH (10 ml) and 50% HCl (10 ml) is heated to 40-50° C. for two hours. Methanol is evaporated off and the residual mixture is treated with NaOH, extracted with toluene. The organic phase is dried, and the solvent removed under vacuum affording 3-amino-phenyl acetylene.

Provenance & Evidence